The Story Chapters Framework for Executive Communication
Find the last obvious point for your audience, then build from there — skip neither the setup nor the basics.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 92%
A model for calibrating where to begin when presenting to executives. Winters frames any piece of work as a story with chapters: the strategy you're working on, the metrics you're improving, the assumptions guiding you, then the new information. Most presenters either start at 'chapter six' (jumping to conclusions without earning the right) or re-explain the whole company strategy (starting with a textbook on English). The fix is to locate the last point that would be completely obvious to this specific audience and begin one step past it.
Origin
Casey Winters' own framing, developed coaching product teams at Eventbrite as Chief Product Officer.
Core principles
- 01Work presented to an exec is a story you must tell from an appropriate starting chapter
- 02You haven't 'earned the right' to tell later chapters if you skip the foundational ones
- 03Over-explaining wastes the scarce minutes before you reach new information
- 04Executive communication is really 'executives communication' — each individual has a different style and different concerns
- 05Questions from executives are usually attempts to learn, not tests to catch you out
How to run it
- 1
Map your work to the story's early chapters
Before presenting, articulate chapter one explicitly: what part of the company strategy you're working on, what metric you're trying to improve, and what assumptions are guiding what you're building.
Pro tip Writing these down in advance means you can free-form confidently from material you know deeply rather than reciting bullet points.
- 2
Find the last obvious point for this audience
Identify the final point in your story that would be completely obvious to the specific person you're addressing. That is your true starting line — anything before it is wasted time.
Watch out Don't start on chapter six (skipping setup) but also don't start with 'a textbook on the English language' by re-explaining what everyone already knows.
- 3
Move from obvious to less-obvious in sequence
From that starting point, walk to things that are progressively less obvious but that the audience can still follow along with, so each step is earned.
- 4
Re-calibrate for each audience
Re-dial the starting chapter for every audience — an individual engineer needs very different things than the CEO or CFO. The same work is a different story to each listener.
Pro tip Treat executive questions as the person trying to understand, not testing you — this changes the whole interaction and removes intimidation.
In the wild
At Pinterest, key strategic topics went through product review with CEO Ben and head of product Jack, who had very different styles. Jack would ask a few data questions early to get context on the problem. If the presenter didn't know those answers, it cast doubt on the entire rest of the meeting because the team lost confidence that the presenter had the right context.
→ Winters learned to coach teams to anticipate the specific early questions each executive would ask and arrive with the data in hand.
Common mistakes
Starting at chapter six
Jumping straight to your conclusion or new information without establishing which strategy, metric, and assumptions frame it — even if that part is right, the audience can't follow because you skipped the first five chapters.
Starting at the beginning of time
Spending the first 20 minutes re-explaining company strategy or who the customer is to people who already know it, using up your limited time before you reach anything new.
Is it for you?
Best for
Product managers and designers presenting to executives, boards, or cross-functional leadership who need to land new information without losing the room.
Not ideal for
Peer or IC-to-IC communication where shared context is already deep and the story framing adds overhead.
From the transcript
“you have to start with chapter one which is you know what part of the company strategy are you working on what metrics are you…”
“many times when non-executives are presenting to execs they'll start on like chapter six”
“you want to you want to find the last point in your story that would be completely obvious to the person you're telling the story…”
“executive communication is actually executives communication you're communicating with individual executives that all have different styles”
From the episode
How to sell your ideas and rise within your company
Casey Winters, Eventbrite